


Slaying Dragons in Gladiator Heels

by SecretGeniusShittyKnight (augopher)



Category: Check Please! (Webcomic)
Genre: F/M, Lardo is a master at makeup, Non-fetishized Crossdressing, Self-Discovery, Shitty really hates his family, gender variant character
Language: English
Status: Completed
Published: 2016-04-23
Updated: 2016-04-23
Packaged: 2018-06-03 17:17:57
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,891
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6619486
Author URL: https://archiveofourown.org/users/augopher/pseuds/SecretGeniusShittyKnight
Summary: <blockquote class="userstuff">
              <p>It started the way all of Shitty’s best plans do, with a mix-up and a wicked idea to piss off his family (elitist and bigoted snobs the lot of them). And if his little masquerade led to transcending to a higher plane of self-awareness, well then.</p><p>That was between him and his mustache.</p>
            </blockquote>





	Slaying Dragons in Gladiator Heels

**Author's Note:**

> All characters, aside from Shitty's roommate who is my own, are creations of Ngozi Ukazu and appear in her brilliant webcomic [Check, Please!](http://omgcheckplease.tumblr.com/post/57705111693)
> 
>  
> 
> This fic was originally just a fleeting idea, but thanks to the encouragement from those on [omgchatplease](http://omgchatplease.tumblr.com/), I went ahead and wrote it.
> 
> This is my take on why Shitty was absent from the latest updates.

It started the way all of Shitty’s best plans do, with a mix-up and a wicked idea to piss off his family (elitist and bigoted snobs the lot of them). And if his little masquerade led to transcending to a higher plane of self-awareness, well then.

That was between him and his mustache.

 

***

 

His alarm had been blaring “Don’t Stop Me Now” at him for at least fifteen minutes before he rolled out of bed with an intense desire to attack a zombie with a pool cue. Yawning, he stretched out his limbs even though they were anything but stiff–falling asleep totally baked had a way of doing that to him. Really, everyone should wake up after that at least once in their life. Transformative, honestly–and shuffled into the kitchen…

Naked as the day he was born.

Though, now that he’d thought about it, was probably not the best idea, seeing as his roommate, Parker, sat on the living room sofa eating his breakfast. The guy took one look at Shitty and groaned. “Oh come on, Shitty! I thought we went over this last week! Please wear pants when you walk around the apartment. Hell, even underwear would be better.”

Shitty waved him off. “Yeah, yeah. Sorry, Parksy. Slipped my mind. To be fair, you seem a bit tense. Perhaps you could try the birthday suit approach. It’s liberating.”

Parker brandished his spoon and shook it at him. “I asked you not to call me that.”

Shitty rolled his eyes and continued to rummage through the cabinets for his Lucky Charms. When he’d moved out of the Haus, his grandmother had been quite insistent that he accept her offer to buy him a condo near Harvard. He’d scoffed at her, stating he’d rather gouge out his eyes with a skate lacer. Instead, he’d opted for a LBGTQ+ friendly area in Jamaica Plain. Yes, this was where he needed to be.

Which led him to where he currently was, sharing a two bedroom with Parker, the most uptight man he’d ever met, and Shitty was best friends with that Canadian Hockey Robot known as Jack Zimmerman. Parker needed to find a way to unwind if you asked him. It would do wonders for his, frankly unhealthy, stress levels. “You just need to relax, Parker, find yourself a hobby that does not involve studying.”

“Relax? For fuck’s sake, Shitty. Just because I’m gay doesn’t mean I want to see your dick!”

Shitty stopped, fingers wrapped around the handle to the fridge, and swallowed hard. “Is that what you think I’m doing? Dude, I’m sorry. I cross my heart and swear on that Holy Grail, that is that silver cup of Lord Stanley, that I was not trying to give you an eyeful because you’re into guys. That would be horrible of me. I just… clothes, man. They feel all kinds of wrong sometimes. I’m more at home au naturale, but I solemnly swear to try harder to remember to at least wear underwear anytime I leave my room. Sorry to make you uncomfortable.”

“Thank you. Underwear, that’s all I ask.”

He yanked open the fridge and stared, forlornly at the lack of dairy related beverages. “We’re out of milk?” he asked, poking his head around the kitchen wall to find his roommate looking quite sheepish.

“Sorry, Shitty. I’ll get more on my way home after class.”

Shitty shrugged and grabbed a handful of dry cereal, shoving it into his mouth. The marshmallows lost some of their innate charm without milk. “Wholly unsatisfying,” he grumbled.

Instead of gorging himself on sugary breakfast cereal, he retreated to his bedroom to dig through the basket of laundry he’d washed at the corner laundromat last night while he crammed for his midterm in his Contracts class. He donned his lucky [underwear](http://t.umblr.com/redirect?z=https%3A%2F%2Fwww.beeranyone.com%2Fbeer-store%2Fmen-clothing%2Fbeer-boxers&t=Y2FjMzIxYWU5OTUwMTFhYTgzNTRiMWQyMGFiYjE0NTcyYjAyZWNhZCxlSm1GSFplOQ%3D%3D), still pissed he could not find a pair of Wonder Woman boxer shorts (that right there, was the biggest piece of unnecessary clothing gendering he’d ever seen. If he wanted to wear underwear with his favorite superhero on them, then by Gordy, he should be able to do it)and kept rummaging for a pair of pants. From the midst of his various t-shirts, he pulled a lacy, goldenrod colored peasant top. This didn’t belong in here.

For a moment, the briefest of moments–come on now, there were only a few aspects of his appearance that he paid careful attention to, and wardrobe was not one of them–he considered setting it aside to take back to Suds-n-Softener after class. Curiosity and the reality that the notion of him wearing such a garment would absolutely horrify his grandmother got the better of him.

He tugged the shirt over his head, adjusting the sleeves, which clearly seemed meant to be worn off the shoulder, and went to admire himself in the bathroom mirror. “God damn, Shitty. You look like a modern marvel. A sick-flowed, expertly mustachioed, lacy marvel.”

Messenger bag and travel mug of oolong in hand, he made his way out of the apartment, walking right past Parker who shouted, “Shitty, what on Earth are you wearing?” after him as the door shut behind him.

 

***

 

When he sat down in the front row of his first class–what? He may have detested the elitism rampant in the law school, but he was very dedicated to learning all he could so he could one day be the best damn civil liberties lawyer he could be–earning more than a once over from his Torts professor, he felt more settled in his skin than he had since he decided to grow out his flow.

“Mr. Knight, quite the attire you have going on there.”

He scoffed at every one of his professors’ refusal to address him by Shitty, most settling on his surname, with a couple insisting on using the farce that was his given name (Bainbridge, what load of crock _that_ moniker was) instead.

“I’m taking a class from the sociology department. It’s part of my final project.” Lies. Total lies.

Professor Wellington peered underneath his bifocals down his nose at him. “And what, project pray tell, would that be?”

Shitty shrugged. “Oh you know, examining how the gendering of clothing affects one’s academic performance and what it means for social awareness.”

“I see.” That right there, was the tone of disgust Shitty had hoped to hear from his family when he’d put on the shirt. It made him want to expand on this idea even more.

“I know. It’s going to progress from here. Just you wait. Soon, I’ll be trying out skirts and makeup. Don’t you worry your tenured head over it.” Which what? Where the hell had _that_ come from.

Oh well. In for a penny. In for a pound.

 

***

 

The thing was though, that what started out as a whim, quickly proved to be quite empowering. He soon found himself browsing through Boomerangs, feeling an intense sense of pride at both squashing gender stereotypes and helping charity. He’d gladly throw his family’s money at a store whose proceeds went to help fight AIDS and HIV.

His hands were full of various garments, from a floral print miniskirt; a vintage, red-polka dot, a-line dress; a pink bustier; to a pair of black, lace shorts. Two aisles over, he caught the stare of an older woman and steeled himself for a case of judgement when she began to walk towards him. Whatever, he was secure as hell in himself, and he could wear whatever the hell he wanted. Thank you very much.

“You know, I don’t think that shade of pink is really your color,” she said pointing to the bustier. “But I saw a nice plum colored one over there. Perhaps you’d like to try it instead?”

He raised an eyebrow at her. “What? You mean, you’re not going to chastise me with a side of how it’s people like me destroying the social fabric of America?”

She chuckled and patted his arm. “Oh heavens no! It’s none of my business. Besides, my son is a very popular queen in his local drag show. I’d be quite the hypocrite if I judged you. If it makes you happy and isn’t hurting anyone else…what is it you kids say? ‘Keep doin’ you.’ Yeah, that sounds right. Plus, I don’t know if heels are your thing, but if you’re not ethically opposed to shopping at a large business, my David usually has luck finding a good selection of larger sized ladies shoes at Nordstrom.”

He blinked at her, several times, before his brain caught up. “Why…thank you. That’s very helpful of you. Have a ‘swawesome day. You’re an excellent and genuine human being.”

She nodded and let him continue with his shopping. When he walked into the fitting room, he felt a lightness in his chest at the idea that maybe there was hope for society after all.

 

***

“Start at the top of the ear towards the corner of your mouth. Try not to go past the outer corners of your eyes,” the woman on the makeup video instructed him while she demonstrated how to properly contour cheekbones.

“Easy for you to say, Janet,” he scoffed at his computer screen. He glanced at his vanity mirror.. He’d purchased it last week so he could figure this shit out in the comfort of his own bedroom without earning more of Parker’s confused looks as Shitty continued his quest to develop a surefire way to permanently piss off his family.

Well, actually, no.

It had quit being about annoying his upper-crust relatives around the time he decided to wax his legs, you know, just to try it out. Not that he’d ever suggest the women he knew needed to shave in order to be socially acceptable, but if they wanted to rid themselves of unwanted body hair, so be it. Just do it for yourselves, ladies. There was something magical about rubbing his smooth legs against each other as he lay in bed.

Now, it seemed, he had long since moved past trying it out, and into self-awareness. There was something fiercely powerful about wearing a miniskirt and a perfect manicure. Powerful in a way that ‘men’s clothes’ never had been for him. If he were a less educated individual on the subject, he’d be confused as fuck. As it stood, he was slowly figuring out that maybe this was what he’d been missing all along, that variance in his gender expression that took him from Bainbridge Knight to Shitty ‘You Motherfucking Marvel’ Knight.

Not only did he find he liked looking pretty, but he liked the feeling that while rocking a pair of gladiator heels he could fucking fight dragons.

But makeup…Lord Stanley help him, was just something he could not figure out. He’d watched this damn video and countless others dozens of time. Why the hell couldn’t get the hang of it?

His splotchy complexion stared back at him. “I look like Bozo the freaking Clown.”

Angry, frustrated, and growing increasingly despondent over the matter, he jabbed a finger on the ‘x’ at the top of the tab, effectively closing Youtube. Several times now, he simply considered that maybe makeup was just not for him.

He plucked a makeup removing wipe from the dispenser on his dresser, dragging it across his face until all evidence of any cosmetics was gone. There was just no way he was going to master makeup on his own. But who could he ask for help?

Though he may have looked like a person who gave zero fucks when it came to others and the way he looked, the way he dressed, that was not true. Well not completely. He didn’t care one iota about what his relatives thought, but there was a group of people, his chosen family, whose opinions of him he valued deeply. The idea that any of them might decide _this_ , his new look, his whole outlook on life and who he was as a person, was just too weird filled him with abject terror.

That whole devil-may-care demeanor of his, while he first affected it in order to deal with the fact that the Knight’s seemed completely unwilling to understand him, it was purely a façade- a defense mechanism.

Looking back on it, there had always been a small voice in his head that saw a dress, ruffles, and floral prints and appreciated the beauty of them. After some deep reflection, he remembered one instance quite clearly where he’d actually shown hints of the repressed desire to have some feminine finery of his own. The memory had lain buried in the deepest corners of his mind beneath things like hockey, beer, and the way he detested everything his father stood for.

He’d been about seven and was shopping with his mother. Some society dinner, fuck if he understood what kind at the time. For hours, his mother had browsed, looking for that perfect outfit, before they’d ended up in Barney’s at Copley Place. Bored out of his mind, he wandered away from her, not that she’d notice, so engrossed in her search.

The moment he’d seen it, that beautiful dress with fabric draping down to the floor, he needed to touch it. Exquisite and soft, he let that silk slip through his fingers. He’d never before in his life worn something so pleasing to the touch. He’d wanted, God how he’d wanted, and that’s how his mother had found him, his little hands still clutching to the designer evening gown. She’d chastised him in words like ‘what were you thinking?’ and ‘that’s not for you!’ when he’d voiced his desire to wear something soft like that. The tongue lashing continued until they’d gotten home.

It was amazing how he’d made himself repress that memory, mostly out of shame he supposed. Yet after a night of a couple bowls of strong weed, he’d plucked that image from his mind. He’d realized that desire had always been there, but somehow, for all his enlightened thinking, he’d ignored that nagging feeling and stuck to his gender norms. A mistake, he realized that now.

Perhaps that was why he’d never made a move in declaring his feelings for Lardo, he’d been afraid that if she’d known this part of him, she’d reject him.

But, if he were to embrace this new side to his gender, and go into it–as Bitty would say–whole hog, he was going to need to face this obstacle. What was the worst that could happen? For starters, he’d screw up one of the closest friendships he’d ever have, so there was that. If Lardo wanted nothing to do with him after this, he was a big boy, he’d get over it.

Well, probably not, but it wouldn’t be for a lack of trying and a whole lot of booze.

With an uncharacteristic, trembling hand, he picked up his phone, scrolling until he found the contact he needed. It rang three times before Lardo answered.

“About fucking time you called me, Shits. I was beginning to think you’d gone cake eater on us with your new Harvard classmates.”

“I need your help, Lardo. It’s a life or death matter. There will be a train ticket to Boston with your name on it waiting for you at the station. Get here quick.” He winced as he ended the call before she had a chance to say no and did as promised: bought her a ticket.

 

***

 

More nervous than he could ever remember being, Shitty adjusted the pink, heart-shaped sunglasses atop his head, as he stood there in Back Bay Station two hours later in a ruffly, black t-shirt and a pair of daisy-print shorts with a hemline high enough to make Bitty jealous.

When Lardo stepped off the train, looking disheveled and frenzied the likes of which he’d never seen her, she did a triple take before she recognized him. Then, she hurried over and punched him in the shoulder. “You ass! You said it was a life or death matter. I was expecting to have to pay a hefty ransom to get you back from kidnappers! And here I find you looking perfectly fi…” she stopped and took a good long look at him, standing there speechless. When the silence stretched out into an unbearable five minutes, Shitty felt something akin to the way Jack had once described an anxiety attack building in him. Finally, she seemed to get a hold of her mental faculties and put him out of his misery. “So you’re not in danger of great bodily harm?”

“No.” He took a deep breath. “Your mission, should you choose to accept it, is to teach me how in the hell to do my make-up, because if I am going to go out every day looking like a beautiful motherfucking masterpiece, I need my warpaint.”

“This is a new look for you, Shits. I had no idea.”

“Yeah, I didn’t either until I found a shirt in my laundry by mistake. Once I tried it on, there was no going back. So… I guess what I’m saying is, this is me, Shitty Knight, and the way I am supposed to look. Feels right. Or it would feel right if all my attempts at makeup didn’t make me look like a circus clown. But then I thought, you know whose eye makeup game is always strong? One Larissa ‘Lardo’ Duan. Though in hindsight, calling it a life or death situation may have been a bit of an exaggeration.”

Lardo folded her arms across her chest. “What is this, really? Is there another name you’d like me to call you now? Do I need to change my pronouns?”

“I have done as extensive of research as my class-load would allow, and gender variant is what I’ve decided I am. So, will you help me?”

Lardo covered her heart with her hand. “I would be honored to help you, Shitty, my bro-in-arms, undertake the important task of becoming a master of that mysterious thing known as make-up.”

“And that,” he said wrapping an arm around her shoulder, “is why you are the absolute best.”

“I know.”

 

***

 

Lardo placed a piece of tissue on his bottom lip, “Press your lips together for me.” When she’d blotted the excess lipstick from his mouth, she spun Shitty around in his computer chair to face the vanity mirror on his desk. “Looks like making you copy what I did for the right side of your face on the left was the way to teach you. What do you think?”

Shitty blinked, staring at his reflection as though he were seeing himself for the first time. Eyebrows, so perfectly plucked and filled in to perfection had never adorned his face. He had winged eyeliner to end all winged eyeliner, and even the lipstick made his sweet-as-fuck mustache look the best it ever had. He looked fucking phenomenal, and it brought tears to his eyes. Let it never be said that he was not an emotional person. “I look,” he said, his voice, cracking, “like I could slay dragons. I’m so God damned pretty I don’t know what to think right now.”

Lardo ruffled his hair. “The fucking prettiest.”

“Lards, in case I never said it before, but you are a miracle worker and a damn precious gift to the world.”

She squeezed his shoulder. “Aww thanks, Shits. Love you too, bro.”

He rubbed the back of his neck. “Yeah, about that…I get it now, but at the time I didn’t know why I didn’t say anything at graduation. Dude, I’m so fucking gone on you. I don’t think I could properly explain just how gone that is. So…if say, I were to ask you on a date, you know to go to dinner with me, what would you say?”

She smiled, warm and crooked, the kind of grin she didn’t show often, because well, if he hid behind a veil of nonchalance, she hid behind a tough-as-nails armor. Then, she leaned forward and placed a chaste kiss on his forehead. “Well, I’d say I was crazy about you. And so long as dinner includes a friendly game of pool, that sounds like a perfect way to spend an evening.”

 

***

 

“You sure about this?” Lardo asked him from her bedroom at the Haus.

Through his laptop screen, he could see that she’d changed the colors on her walls again, not that it mattered. He was just noticing mundane details as a way to avoid the inevitable. So, instead of dwelling over the suggestive way she’d posed her artist mannequins or the colorful patches sewn on her curtains, he took a deep breath. “Yeah.”

The video shook with her every step as she carried her tablet downstairs. She sat it down on the kitchen counter, and soon the little icon that indicated another call connecting, appeared at the bottom of the screen.

“Oui, allô?” Jack answered without looking at his screen.

“Jack Motherfuckin’ Zimmerman, how the hell are you?”

“Shitty? Sorry, I thought it was my dad calling. He usually calls right about now.” Jack looked at the screen, blinked a few times, then shrugged as if seeing Shitty in a lacy, blue camisole and a full face of makeup was old hat by now. “What’s up? And why is Lardo in the call too?”

“All in good time, bro. I only want to give this spiel once.”

“Okay.” Jack lowered his brows at him, studying his face like he was searching for hidden meaning in his words.

“SHITTTTTTTTTY!” The raucous chorus of voices from his former teammates filled his room, and he looked up to see everyone piled on or around the health hazard known as the Haus couch.

“Hey, guys. Long time no see.” He swallowed hard. “So, I’ve been going through some stuff…”

He explained–to absolute silence from everyone–his newfound outlook on gender and how it fit into his life. When he’d finished speaking, he waited, teary-eyed, shaking a bit in his skin at how they might react.

“That’s cool, bro,” Nursey, ever calm and relaxed, spoke first. “Diggin’ your flow, man. You put some wave in it?”

“Um…no? It’s a curling iron.”

“Looks nice.”

And that was it. After Nursey had broken the ice, the rest of the team began to voice their approval of his change in gender expression. When he ended the Skype session thirty minutes later, with Lardo promising to call him back later for an ‘important art lesson’, which was totally code for extra-curricular activities of the salacious nature, Shitty flopped back on his bed and stared up at the ceiling, his chest full to bursting.

Whatever happened with his blood relatives from here on out was irrelevant. His family, his _true_ family loved and accepted him exactly the way he was. And that was pretty ‘swawesome indeed.

 

***

 

Shitty finished taping the flyer to the inside of the window at Suds-N-Softener before stepping back to admire his handiwork.

 

 

“Yep, that’s one fine ass piece of poster work, if I do say so myself.” Then, he picked up his vintage handbag and walked out the front door, the heels of his patent leather pumps clicking and clacking against the pavement. 

Societal gender norms be damned.

 

 

**Author's Note:**

> Come visit me on [Tumblr](http://secretgeniusshittyknight.tumblr.com/)


End file.
